A wager with an asshole

Author's note: thanks agin for your continued support. I know I have a tendency to swap POV from time to time but I hope you can bear with it. I just write it out as I see it. I'll try doing an overhaul taking out typos and small adjustments here or there but for now I hope you guys enjoy! Please make sure to like the chapters so that the story gets seen more by others! Thabks for the support and feel free to leave a comment with things you guys want to see happen. If I can I will do my best to incorporate your requests!

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You leave the pokemon center munching on the apple you took from the breakfest bar.

"$4 for an apple, arceus I forgot how expensive they are."

Heading north, you begin making your way out of town when you see a police officer in from of a large building. She appeared to be taking a statement. As you pass by you manage to overhear her.

"Its obvious team rocket is behind this most heinous crime!"

Team rocket? Those gangsters who were searching for fossils? Don't get me wrong they sounded like petty theives, but you wouldn't go as far as say heinous. Throwing it from your mind you continue walking.

"Yo leaf! You still struggling along back here? I'm doing great! I caught a bunch of STRONG and SMART pokemon. Let's see what pathetic pokemon you managed to catch." You groan as Gary steps out from a corner and challenges you. He was still a asshole.

"Depends gary, are you going be a cheapskate and not give me the money I earned when I kick your ass? Last time you couldnt even pay me the full amount." You laugh as he turns a shade of crimson.

"You mean when I tricked you into taking less. I'll make you a deal! If you manage to beat me somehow, I'll give you $1000 this time. However, if I win you have to drop to your knees and suck my cock. Shouldn't be too hard since I'm sure you are used to it by now!" He laughed this time as he cupped his shorts. My mind instantly flashed to last night to me sucking Arbok's giant pair of cocks. A crimson blush lit across my face.

"New deal, if you win, I'll suck your cock. If I win however, I want $3,000." His eyes went wide at the amount.

"Don't tell me your scared I'll kick your ass AGAIN!" I laughed as I called charmeleon out from his pokeball.

"Why you little bitch! You are going down! Go pidgeotto!"

"Alright charmeleon! Use smokescreen and shred that bird!" Immediatley a thick plume of smoke billowed out of charmeleon's mouth. Pidgeotto backing up trying to stay out of the cloud.

"Pidgeotto! Use gust to blow away the smoke!" Gary's voice cried out.

Pidgeotto began flapping its wings back and forth driving the smoke away. As the haze dissapated, charmeleon burst out of the clouds to land on pidgeotto, his metal claws ripping into the bird's wings. Unable to carry their weight, pidgeotto fell and hit the ground with a loud thud. Charmeleon got up no worse for wear. The same couldn't be said for pidgeotto.

"Stupud bird, you are such an embarrassment. Go squirtle! Kick this fire lizard's butt." Gary called back pidgeotto and sent out the familiar water turtle pokemon.

"Way to go charmeleon though come on back. Go Arbok!!"

In a burst of light the purple cobra was now leering over the tiny turtle, glaring menacing down at the pokemon. Clearly intimidated, the turtle took a step back, before stopping all at once as the glare from arbok reached squirtle. Squirtle immediately withdrew into his shell, pulling his arms and legs inside the shell to protect himself. Arbok slowly coiled around the shell and began squeezing tighter and tighter. However he couldn't break the shell. With a command, I had him begin using his fangs on any piece of flesh that wasn't tucked into the shell. Namely the tail.

"Get out of there you coward and fight! You are going to cost me alot of money!" Gary was funing now.

Squirtle did his best. He tried leaving the shell only to be bit down upon by arbok's fangs. Eventually he stopped coming out.

"Release him arbok. I think he is ****." Arbok slithered off off squirtle and after a minute of him not coming out, gary returned squirtle to his pokeball.

"I'm not finished yet. Go abra!"

This fight lasted even shorter. One bite from Arbok's powerful jaws and abra was out. Abra was quickly followed by Gary's last pokemon, a rattata. Frozen in place with fear feom Arbok's glare, one quick bite and the match was over.

Gary was infuriated. He was swearing up and down at his Pokémon. I went forward and hugged arbok.

"Thabks for your hard work out there. You were awesome. I'll be sure to thank you properly later tonight." I whispered the last half to arbok before returning him to his pokeball.

"Well that is the match. I believe you owe me $3,000. Unless you want to back out. Luckily for me there is a police officer right over there."

"Ughhh alright! Fine! Take your money and leave."

"Not so fast! You shorted me last time. Count it out for me. Unless you want my arbok to get rough?" I rested my hand against Arbok's pokeball, clearly testing Gary. He grimmaced and pulled out his wallet and began counting out $3,000. As soon as the money was in my hand he began backing away.

"Next time I won't settle for a blowjob. I'll be fucking you as payback for this. Don't you forget it!" He ran off into cerulean city.

"Good riddance asshole. But thanks for the cash!"